Identification

Name
Ceftazidime
Accession Number
DB00438  (APRD00857)
Type
Small Molecule
Groups
Approved
Description

Semisynthetic, broad-spectrum antibacterial derived from cephaloridine and used especially for Pseudomonas and other gram-negative infections in debilitated patients.

Structure
Thumb
Synonyms
  • CAZ
  • Ceftazidim
  • Ceftazidima
  • Ceftazidime
  • Ceftazidime anhydrous
  • Ceftazidimum
External IDs
CAZ / GR 20263
Product Ingredients
IngredientUNIICASInChI Key
Ceftazidime pentahydrate9M416Z9QNR78439-06-2NMVPEQXCMGEDNH-TZVUEUGBSA-N
Ceftazidime sodiumCMC30V039K73547-61-2JEEWDSDYUSEQML-ROMZVAKDSA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftazidime and DextroseInjection, solution1 g/50mLIntravenousB. Braun Medical Inc.2011-06-13Not applicableUs
Ceftazidime and DextroseInjection, solution2 g/50mLIntravenousB. Braun Medical Inc.2011-06-13Not applicableUs
Ceftazidime for Injection BPPowder, for solution1 gIntramuscular; IntravenousSterimax Inc2015-05-28Not applicableCanada
Ceftazidime for Injection BPPowder, for solution2 gIntravenousSterimax Inc2015-05-29Not applicableCanada
Ceftazidime for Injection BPPowder, for solution6 gIntravenousSterimax Inc2015-06-08Not applicableCanada
Ceftazidime for Injection, BPPowder, for solution3 gIntravenousSterimax Inc2015-06-08Not applicableCanada
Ceftazidime for Injection, USPPowder, for solution6 gIntravenousFresenius Kabi1991-12-31Not applicableCanada
Ceftazidime for Injection, USPPowder, for solution1 gIntramuscular; IntravenousFresenius Kabi1991-12-31Not applicableCanada
Ceftazidime for Injection, USPPowder, for solution2 gIntravenousFresenius Kabi1991-12-31Not applicableCanada
Ceptaz Inj 10gm/vialPowder, for solution10 gIntravenousGlaxo Canada Inc1993-12-312001-11-07Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CeftazidimeInjection, powder, for solution2 g/1IntravenousSandoz2008-05-15Not applicableUs
CeftazidimeInjection, powder, for solution6 g/30mLIntravenousSagent Pharmaceuticals2008-05-15Not applicableUs
CeftazidimeInjection, powder, for solution6 g/100mLIntravenousWG Critical Care, LLC2013-01-31Not applicableUs
CeftazidimeInjection, powder, for solution1 g/1Intramuscular; IntravenousSandoz2008-05-15Not applicableUs
CeftazidimeInjection, powder, for solution200 mg/mLIntravenousSandoz2008-05-15Not applicableUs
CeftazidimeInjection, powder, for solution1 g/20mLIntramuscular; IntravenousWG Critical Care, LLC2013-01-31Not applicableUs
CeftazidimeInjection, powder, for solution1 g/1Intramuscular; IntravenousSagent Pharmaceuticals2008-05-15Not applicableUs
CeftazidimeInjection, powder, for solution2 g/20mLIntravenousWG Critical Care, LLC2013-01-31Not applicableUs
CeftazidimeInjection, powder, for solution2 g/1IntravenousSagent Pharmaceuticals2008-05-15Not applicableUs
TazicefInjection, powder, for solution6 g/1IntravenousHospira, Inc.1986-03-06Not applicableUs
International/Other Brands
Cefzim (Pharco B International) / Ceptaz / Fortum (GlaxoSmithKline) / Tazidime / Veltadim (Novell)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AvycazCeftazidime (2 g/1) + Avibactam sodium (.5 g/1)Powder, for solutionIntravenousAllergan2014-12-26Not applicableUs
Zavicefta Solution for InfusionCeftazidime (2000 mg) + Avibactam (500 mg)Powder, for solutionIntravenousAstra Zeneca Ab2016-06-24Not applicableEu
Categories
UNII
DZR1ENT301
CAS number
72558-82-8
Weight
Average: 546.576
Monoisotopic: 546.099138468
Chemical Formula
C22H22N6O7S2
InChI Key
ORFOPKXBNMVMKC-DWVKKRMSSA-N
InChI
InChI=1S/C22H22N6O7S2/c1-22(2,20(33)34)35-26-13(12-10-37-21(23)24-12)16(29)25-14-17(30)28-15(19(31)32)11(9-36-18(14)28)8-27-6-4-3-5-7-27/h3-7,10,14,18H,8-9H2,1-2H3,(H4-,23,24,25,29,31,32,33,34)/b26-13-/t14-,18-/m1/s1
IUPAC Name
1-{[(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-carboxylato-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
SMILES
[O-]C(=O)C1=C(CS[[email protected]]2([H])[[email protected]](NC(=O)C(=N/OC(C)(C)C(O)=O)\C3=CSC(N)=N3)C(=O)N12)C[N+]1=CC=CC=C1

Pharmacology

Indication

For the treatment of patients with infections caused by susceptible strains of organisms in the following diseases: lower respiratory tract infections,skin and skin structure infections, urinary tract infections, bacterial septicemia, bone and joint infections, gynecologic infections, intra abdominal infections (including peritonitis), and central nervous system infections (including meningitis).

Structured Indications
Pharmacodynamics

Ceftazidime is a semisynthetic, broad-spectrum, beta-lactam antibiotic for parenteral administration. Ceftazidime is bactericidal in action exerting its effect by inhibition of enzymes responsible for cell-wall synthesis, primarily penicillin binding protein 3 (PBP3). A wide range of gram-negative organisms is susceptible to ceftazidime in vitro, including strains resistant to gentamicin and other aminoglycosides. In addition, ceftazidime has been shown to be active against gram-positive organisms. It is highly stable to most clinically important beta-lactamases, plasmid or chromosomal, which are produced by both gram-negative and gram-positive organisms and, consequently, is active against many strains resistant to ampicillin and other cephalosporins. Ceftazidime has activity against the gram-negative organisms Pseudomonas and Enterobacteriaceae. Its activity against Pseudomonas is a distinguishing feature of ceftazidime among the cephalosporins.

Mechanism of action

The bactericidal activity of ceftazidime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).

TargetActionsOrganism
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Pseudomonas aeruginosa
APenicillin-binding protein 2
inhibitor
Pseudomonas aeruginosa
APenicillin-binding protein 2
inhibitor
Escherichia coli (strain K12)
ND-alanyl-D-alanine endopeptidase
inhibitor
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Absorption

The absorption of ceftazidime is directly proportional to the size of the dose.

Volume of distribution
Not Available
Protein binding

< 10%

Metabolism
Not Available
Route of elimination

The elimination of ceftazidime by the kidneys resulted in high therapeutic concentrations in the urine.

Half life

Half-life, following IV administration, is approximately 1.9-hours. Since ceftazidime is eliminated almost solely by the kidneys, its serum half-life is significantly prolonged in patients with impaired renal function.

Clearance
  • 115 mL/min
Toxicity

Ceftazidime overdosage has occurred in patients with renal failure. Reactions have included seizure activity, encephalopathy, asterixis, neuromuscular excitability, and coma.

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolCeftazidime may increase the anticoagulant activities of Acenocoumarol.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Ceftazidime.Investigational
ChloramphenicolThe therapeutic efficacy of Ceftazidime can be decreased when used in combination with Chloramphenicol.Approved, Vet Approved
ClorindioneCeftazidime may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCeftazidime may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCeftazidime may increase the anticoagulant activities of Diphenadione.Experimental
Ethyl biscoumacetateCeftazidime may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCeftazidime may increase the anticoagulant activities of Fluindione.Investigational
PhenindioneCeftazidime may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonCeftazidime may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Ceftazidime.Approved
ProbenecidThe serum concentration of Ceftazidime can be increased when it is combined with Probenecid.Approved
TioclomarolCeftazidime may increase the anticoagulant activities of Tioclomarol.Experimental
WarfarinCeftazidime may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Ronald C. Browning, Melvin G. Pleiss, Jr., "Crystallization process for ceftazidime derivative." U.S. Patent US4659813, issued May, 1982.

US4659813
General References
Not Available
External Links
Human Metabolome Database
HMDB14582
KEGG Drug
D07654
KEGG Compound
C06889
PubChem Compound
5481173
PubChem Substance
46506143
ChemSpider
4587145
BindingDB
50420259
ChEBI
3508
ChEMBL
CHEMBL44354
Therapeutic Targets Database
DAP000433
PharmGKB
PA448861
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Ceftazidime
ATC Codes
J01DD52 — Ceftazidime, combinationsJ01DD02 — Ceftazidime
AHFS Codes
  • 08:12.06.12 — Third Generation Cephalosporins
FDA label
Download (360 KB)
MSDS
Download (28 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedBasic ScienceHealthy Male Volunteers1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentCystic Fibrosis (CF)1
1Not Yet RecruitingBasic SciencePharmacokinetics of Avycaz in ICU Patients1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentComplicated Urinary Tract Infections2
2CompletedTreatmentPneumonia1
2Unknown StatusTreatmentPseudomonas Aeruginosa Meningitis1
2, 3TerminatedTreatmentAscites / Liver Cirrhosis / Nosocomial Spontaneous Bacterial Peritonitis1
3CompletedTreatmentPneumonia1
3RecruitingTreatmentEnterobacteriaceae Infections1
4CompletedNot AvailableCystic Fibrosis (CF)1
4CompletedNot AvailablePerforated Appendicitis1
4CompletedPreventionPancreatitis1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentCystic Fibrosis (CF) / Pseudomonas Aeruginosa / Pulmonary Exacerbation1
4Unknown StatusTreatmentCystic Fibrosis (CF)1
4Unknown StatusTreatmentInfection NOS1
Not AvailableCompletedTreatmentCeftazidime / Ciprofloxacin / Pediatrics / Voriconazole1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentPeritoneal Dialysis Associated Peritonitis1
Not AvailableEnrolling by InvitationBasic ScienceCystic Fibrosis (CF)1
Not AvailableNot Yet RecruitingNot AvailableNewborn; Infection1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cyanide Poisoning / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Edema / Epilepsies / Feeling Anxious / Flu caused by Influenza / Gastroparesis / GYNAECOLOGICAL INFECTION / Headaches / Herpes Simplex Virus / Hospital-acquired bacterial pneumonia / Hypercholesterolaemia / Hyperlipidemias / Hypertensive / Infantile Hemangiomas / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Migraines / Muscle Spasms / Nausea / Opioid Addiction / Pain / Plague / Pneumonia / Prophylaxis / Psittacosis / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Stable Angina (SA) / Thromboprophylaxis / Thrombosis / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingTreatmentCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentLow-output External Gastrointestinal Fistula1
Not AvailableUnknown StatusTreatmentBurkholderia pseudomallei infection1
Not AvailableUnknown StatusTreatmentPeritonitis1

Pharmacoeconomics

Manufacturers
  • Acs dobfar spa
  • Aurobindo pharma ltd
  • Wockhardt ltd
  • Glaxosmithkline
  • Hospira inc
  • Eli lilly and co
  • Baxter healthcare corp
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntramuscular; Intravenous1 g/1
Injection, powder, for solutionIntramuscular; Intravenous1 g/20mL
Injection, powder, for solutionIntravenous2 g/20mL
Injection, powder, for solutionIntravenous2 g/1
Injection, powder, for solutionIntravenous200 mg/mL
Injection, powder, for solutionIntravenous6 g/30mL
Injection, powder, for solutionIntravenous6 g/100mL
Injection, solutionIntravenous1 g/50mL
Injection, solutionIntravenous2 g/50mL
Powder, for solutionIntravenous3 g
Powder, for solutionIntravenous10 g
Injection, powder, for solutionIntramuscular; Intravenous100 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous111 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous170 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous200 mg/mL
Injection, powder, for solutionIntramuscular; Intravenous56 mg/mL
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous20 mg/mL
Injection, solutionIntravenous20 mg/mL
Injection, solutionIntravenous40 mg/mL
Powder, for solutionIntramuscular; Intravenous1 g
Powder, for solutionIntravenous2 g
Powder, for solutionIntravenous6 g
Powder, for solutionIntramuscular; Intravenous500 mg
Injection, powder, for solutionIntramuscular; Intravenous2 g/1
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous6 g/1
Powder, for solutionIntravenous1 g
PowderIntramuscular; Intravenous500 mg
Powder, for solutionIntravenous
Prices
Unit descriptionCostUnit
Fortaz 6 g/vial150.11USD vial
Ceftazidime 6 gm vial97.05USD vial
Fortaz 6 gm vial82.8USD vial
Fortaz 2 g/vial50.01USD vial
Tazicef 6 gram vial29.88USD vial
Fortaz 2 gm add-vantage vial28.93USD vial
Fortaz 2 gm vial28.45USD vial
Fortaz 1 g/vial25.44USD vial
Ceftazidime 2 gm vial19.97USD vial
Fortaz 1 gm add-vantage vial14.71USD vial
Fortaz 1 gm vial14.23USD vial
Tazicef 2 gram vial10.66USD vial
Ceftazidime 1 gm vial10.46USD vial
Ceftazidime-sodium carb powder6.27USD g
Tazicef 1 gram vial4.57USD vial
Fortaz-iso-osmot 2 gm/50 ml0.62USD ml
Fortaz-iso-osmotic 1 gm/50 ml0.34USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7112592No2002-02-242022-02-24Us
US8178554No2001-07-242021-07-24Us
US7612087No2006-11-122026-11-12Us
US8471025No2011-08-122031-08-12Us
US8835455No2010-10-082030-10-08Us
US8969566No2012-06-152032-06-15Us
US9284314No2012-06-152032-06-15Us
US9695122No2012-06-152032-06-15Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)103-113O'Callaghan, C.H., Livermore, D.G.H. and Newall, C.E.; British Patent 2,025,398; January 23, 1980; assigned to Glaxo Group Ltd.
water solubility396 mg/LNot Available
logP-1.60HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00573 mg/mLALOGPS
logP-1.2ALOGPS
logP-4.1ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)2.77ChemAxon
pKa (Strongest Basic)4.26ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area191.22 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity143.88 m3·mol-1ChemAxon
Polarizability51.06 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8406
Blood Brain Barrier-0.9857
Caco-2 permeable-0.7235
P-glycoprotein substrateSubstrate0.8593
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IIInhibitor0.6684
Renal organic cation transporterNon-inhibitor0.8311
CYP450 2C9 substrateNon-substrate0.8404
CYP450 2D6 substrateNon-substrate0.8155
CYP450 3A4 substrateSubstrate0.5897
CYP450 1A2 substrateNon-inhibitor0.8112
CYP450 2C9 inhibitorNon-inhibitor0.7396
CYP450 2D6 inhibitorNon-inhibitor0.8758
CYP450 2C19 inhibitorNon-inhibitor0.7009
CYP450 3A4 inhibitorNon-inhibitor0.8354
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7222
Ames testNon AMES toxic0.7979
CarcinogenicityNon-carcinogens0.8252
BiodegradationNot ready biodegradable0.9951
Rat acute toxicity1.6048 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9938
hERG inhibition (predictor II)Non-inhibitor0.659
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-1900000000-35c537be0b49e8347500
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-3900000000-f8108350d09aeabb208f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0pb9-9600000000-3a117de626550cd6bd1e
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-9200000000-42d1f87964b083915995
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-9100000000-9b08b7904165504611b6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014j-0115900000-d76de6ad1809c0528b8c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-1910000000-cb7ea1c7b4b139a7336e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01tl-3900000000-07fadc61e1b566ec14ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-5900000000-e92b85ec9fabd9a4c1fe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-004i-7900000000-548213f534e499ba783b

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / Pyridinium derivatives / 2-amino-1,3-thiazoles / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids
show 13 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / Dicarboxylic acid or derivatives / 1,3-thiazol-2-amine / Pyridine / Pyridinium / Azole
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, oxime O-ether (CHEBI:3508)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan fr...
Gene Name
ftsI
Uniprot ID
P0AD68
Uniprot Name
Peptidoglycan synthase FtsI
Molecular Weight
63876.925 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q75Y35
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
45209.84 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
mrcA
Uniprot ID
P02918
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
93635.545 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
pbpA
Uniprot ID
Q8DR59
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79700.9 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
mrcB
Uniprot ID
P02919
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
94291.875 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
General Function
Peptidoglycan glycosyltransferase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
ponB
Uniprot ID
Q9X6W0
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
85486.615 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbpA
Uniprot ID
Q9X6V3
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
72212.855 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
Gene Name
mrdA
Uniprot ID
P0AD65
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
70856.1 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
No
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation.
Gene Name
pbpG
Uniprot ID
P72161
Uniprot Name
D-alanyl-D-alanine endopeptidase
Molecular Weight
34046.065 Da
References
  1. Hayes MV, Orr DC: Mode of action of ceftazidime: affinity for the penicillin-binding proteins of Escherichia coli K12, Pseudomonas aeruginosa and Staphylococcus aureus. J Antimicrob Chemother. 1983 Aug;12(2):119-26. [PubMed:6413485]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
  2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33